


We Can Work It Out

by JackTrades



Series: I Like To Watch [6]
Category: Supernatural
Genre: Masturbation, Multi, Porn, more tags to come
Language: English
Status: Completed
Published: 2016-07-30
Updated: 2016-08-11
Packaged: 2018-07-27 16:42:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,941
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7626187
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Dean learns that Sam's deviant tendencies are just like his own.</p>
            </blockquote>





	1. Chapter 1

Dean precariously managed to stack the case of beer and two pizzas he bought with enough precision to get the motel room key card out of his front jeans pocket. He gave himself a satisfied smirk when he stood upright with the flimsy strip of plastic in hand. He was in the middle of the parking lot in their decent enough motel in Maryland. He caught the middle aged woman from four rooms down giving him a look as she herded three dirt-covered brats to the general direction of their room. He thought, ‘ _ Fuck you, lady. It doesn't require two trips _ .’ Dean knew the brats would be trampling back and forth from their room to the vending machines, tucked away in an alcove next to the Winchesters’ room, for the next few hours. Just like the last two nights.

 

Luckily for them, Dean thought ahead and got enough beer for Sam and him to be too drunk to care that the stampede continued all night. They were in a lull between cases and figured this was as good a place as any to stake out a new job. Dean liked it here because the room was really more of a suite; it was spacious enough to get away from each other if they need breathing room. Sam said he liked the place because the shower head is higher than most showers and it had a curtain instead of doors. This meant Sasquatch could stand like an almost normal human to shower. Dean fumbled the key twice before successfully unlocking the door. He burst through the door and immediately hooked his toe behind it to kick it shut. The pissed off, decidedly high pitched, “Dude!” from Sam hadn't immediately registered. 

 

Dean didn't even look at Sam. He continued on his mission to deposit the pizzas on the kitchen table and the beers in the mini fridge. Dean grumbled, “What? I didn't slam the door. I've got my hands full. I was even nice and ordered you that gross broccoli, peppers, and onions white pizza that you like.” Dean turned to Sam and immediately threw his hand over his face in exaggerated disgust. “Really?” Sam was attempting to cover himself and failing. His erect cock was out in the open and his laptop was next to him on the bed. “There's a code, man! All you had to do was leave a warning sign.”

 

Sam barked back, “I did, asshole!” He angrily pointed to the tie half sticking out of the door. It was clearly hooked around the doorknob outside and stuck in the door from Dean's swift kick. This had been the ‘do not enter’ sign for years for anything from a hook up to epic burrito farts to keep each other away from the room. 

 

Dean had been so busy balancing his arm load of stuff that he did not notice the tie. “Oh.” Dean felt bad. Sincerely bad. Dean sputtered, “I'm really sorry. Shit, sorry. I'll leave and -”

 

Sam huffed, “Don't bother. I'm not into it anymore.” He tucked himself into his boxers and started to pull his jeans up.

 

Dean scrambled, “No! Seriously, I'll go. It's bad enough I interrupted. I won't be responsible for you blue balling yourself.” 

 

Sam shot back, “Myself? It's your fault. I didn't do anything to myself.” He rolled off the bed, stood, zipped up, and buckled his belt. “Besides, I'm kinda hungry.”

 

Dean scoffed, “This is not okay!”

 

“Oh? Are you offering to do something about it?” Sam joked as he went to the door to retrieve his tie. Dean sputtered and came up with nothing creative in response. Sam rolled the tie and stuffed it in his duffle bag. Dean tossed him a beer as he turned towards the table. Sam caught it and cracked it open. “Thanks.” 

 

They both wolfed down two slices before attempting to converse again. Dean started, “I'm serious, Sammy, if you don't get off tonight I will hold myself personally responsible.” 

 

Sam laughed, “Is it fucked up that I don't question your level of interest in me getting off anymore?” Both of them knew they passed ‘fucked up’ a long time ago. 

 

Dean shrugged but says nothing else. He finished his beer and wordlessly asked Sam if he wanted another by shaking his empty can and pointing to Sam. Sam nodded. Dean got two more cans out of the fridge. Dean took a few sips before speaking, “I'm serious. I'll leave if you just want to rub one out.”

 

Sam sighed long and deep from his chest. “It's not a big deal.”

 

“Yes it is!” 

 

“It really isn't.” It annoyed Sam that Dean won't let this drop. Dean got up and grabbed Sam's laptop. He stormed over to the couch and put the laptop on the coffee table in front of it. He made a show of undoing his belt buckle, popping his jeans button, and unzipping his fly. Sam put down his beer and looked at Dean like he thought Dean got hit by some bad hoodoo. “Uhhhh, Dean? What are you doing?” 

 

Dean flopped onto the couch and pat the cushion next to him. He gave Sam a challenging stare with that shit eating grin that Sam hated. “Saddle up! Family fun time.”

 

Sam scoffed, “Dude, no.”

 

“Oh come on!” Dean leaned back, confident. “It will be just like when -”

 

Sam cut him off, “Don't say it'll be just like we were kids. Newsflash: we're not kids anymore.” 

 

Dean shrugged, “Yeesh, it's not like we haven't done worse over the last couple of years. It's been at least a handful of times that we have watched each other fuck. What's the big deal if we jerk off together?” Sam was unfazed. Dean reached for the laptop. “Or are you just afraid of me finding out what you are jerking off to?” 

 

Sam slapped the lid shut, “Knock it off. This is just some roundabout way to make fun of me.”

 

Dean pouted, “Would I do that?”

 

Sam was not amused, “Yes. You absolutely would.”

 

Dean laughed and admitted, “Fine, I totally would. That's not what I'm doing now.” Sam was still eyeing him like Sam doesn't trust him. Dean upped the effort, “Seriously though, whatever you were getting off to is nothing to be embarrassed about. Different strokes for different folks, right?” Dean stroked himself over his jeans to punctuate his point. This was either a great idea or a horrible idea…

 

Sam was weary, “How is this gonna work?”

 

Dean settled further into the couch. “You sit your ass down, we watch a video, and we jerk off. It's not brain surgery, Sam.”

 

Sam assessed the way they would be situated, “Dean, we would be right on top of each other. That couch is barely big enough for us to sit and watch TV.” 

 

Dean smirked, “What are you afraid of bumping elbows or something?”

 

Sam dryly replied, “Or something.”

 

“Lighten up.” Sam started to make a bitchy face at Dean. Dean added, “I'll keep my hands to myself. I promise.” 

 

Sam assessed his options. If he legitimately wasn't interested, he could have squashed this immediately. “Move to the other side of the couch.”

 

Dean laughed, “You do it left handed? Weirdo.”

 

“Dean!”

 

“Oh calm down. Grab some beers while you're up.”

 

Sam begrudgingly grabbed two fresh bottles and opened them. He had the foresight to also grab the stack of napkins from the dining table. He handed Dean one beer and plunked down on the couch next to Dean. Dean silently celebrated his victory but covered it by taking a large swig of beer. Sam picked up his laptop and stopped opening it when Dean peered over. “No! You don't get to see until I close out what I was watching before.” 

 

“It can't be that bad.” After a brief glaring contest Dean conceded, “Special - one time offer - I see what it is and I won't make fun of you.” Sam glared but opened the screen and Dean was surprised what was paused on the screen. “Huh, never had you pegged as a strap on porn guy. Heh - ‘pegged’...” Dean trailed off as he laughed at his unintentional wording of his comment. 

 

Sam slapped the lid shut again, “You said you wouldn't make fun of me.” 

 

Sam tried to stand but Dean pulled him back down. Dean wasn't in the mood to wrestle him back down so he goes deadweight instead. Dean insisted, “I wasn't making fun. It's just an observation. I didn't think you'd be into that stuff. You never mentioned it before. That's all.” 

 

Sam sat back down and glared again, “Why would this come up in conversation? Was I just supposed to say, ‘Hey Dean, I think I really enjoy watching dudes get railed in porn?’” 

 

Dean shrugged, “Yeah? What the hell would I care? It's cool if you're into it. It's fun.”

 

“Fun?” 

 

Dean couldn't tell if that tone was condescending or skeptical. It made him fidget a little. “Yeah.”

 

Now Sam was curious, “Do you mean the porn is fun or the butt stuff during actual sex?”

 

Dean was fully fidgeting now. Dean's hesitation to answer is clear in his voice, “... both?”

 

Now it was Sam's turn to grill Dean, “Since when do you take it in the ass? That's something  _ you  _ never mentioned.”

 

“Look, I was 19 okay. You remember my girlfriend Rhonda?” 

 

Sam nodded and waited for more information. 

 

Dean sat up straighter, “Rhonda was a freak in bed. I mean, the women I fuck now really ought to send her thank you cards. She really put me through my paces to be like her… what did she call me?” Dean got lost in thought before he finally remembered, “Sex doll! That's what she called me.”

 

“But wouldn't a sex doll just lay there and do nothing?”

 

“Shut up, Sam! I get that the name doesn't make sense but she was all about that femdom stuff. I got really wrapped up in it when I was with her.” Sam was not entirely surprised by that. He knew Dean was a whore for praise and fulfilling demands for women in bed. This wasn't really a stretch. “So one night she convinced me to do it. It was fun but I didn't do it again with her before we broke up and moved to the next job.”

 

“And you never did it again?”

 

Dean shifted again, “I mean, I fooled around with a few guys in my early 20s but I didn't like it. It's not the same.” 

 

Sam wasn't surprised by that. Dean had been known to fool around with guys from time to time. “But never another chick -”

 

“Oh yeah, that's a great pickup line!” Dean yelled, “‘Hi, I'm Dean. Would you be interested in fucking me in the ass?’ No! I only had a couple steady hookups and even less girlfriends. They were not into that stuff in the slightest.” Dean grinned, “What about you? Besides that dominatrix lady - have you had any action like that?”

 

Sam smiled, “Nah. Jess was my only serious girlfriend and she had a couple kinky things she wanted to try. Nothing that screamed that I should ask her about that.” 

 

Dean threw an arm around Sam, “Now that we have that out of the way, what are we watching?”

 

Sam huffed, “This is a lot less action than I was hoping for. If you didn't freaking barge in on me, I would have changed it. What are you in the mood for?”

 

“Dude, I'm always horny. I'm not picky about what we watch.” Dean leaned back and decided to let Sam pick. If it sucked, Dean could make fun of his terrible taste in clip selection. 

 

Sam knew Dean's porn preferences - mostly because Dean was incapable of closing out the Internet browser before returning his laptop. The thought of clearing the browser history rarely occurred to Dean… at least when Dean borrowed Sam's computer. Sam navigated to one of his favorite free clip sites and went from there. Very little effort to find a threesome with the woman in the middle being a cute Asian woman. She was definitely Dean's type of girl from the porn Sam had stumbled upon previously. Twelve minutes should be plenty of time for their collective goal to be achieved.

 

Thankfully the clip didn't have any preamble or bullshitting around. It jumped right into all three naked as the woman tried to alternate between blowing each guy. Sam stroked himself through his jeans while Dean opted to shove his own pants and boxers out of the way. Dean threw his arm around the back of the couch to keep it out of Sam's way. 

 

Sam didn't tease himself for long. His erection made a comeback quickly. On the screen the two men pushed the woman to her hands and knees on a couch. One took her from behind while the other alternated between letting her jerk him off and thrusting into her mouth. She gave exaggerated loud moan when her mouth wasn't full. 

 

Sam huffed, “The fake moaning is annoying. Why do they do that in porn?”

 

Dean snapped, “Inappropriate time for conversation, bitch.”

 

Sam muttered, “Jerk,” out of habit. 

 

The fake moaning and close up shots of the woman's vagina seemed to get Dean to move his hand at a faster pace. He unconsciously let out a moan that Sam knew well. It was the one he made when he thought he was being quiet in the bed next to him in the motel as he jerked off. The one where he was about to blow his load. Sam saw no reason to not speed up himself. 

 

Dean finished first. He spilled over his fist and legs. He sagged back. His arm over the back of the couch went lax and brushed against Sam. Dean idly ran his fingers through Sam's hair before Sam slapped his arm away, “Stop it, Dean!” 

 

Dean was too out of it to notice Sam's annoyance. Sam lasted a minute longer and came with a shout that he muffled with his free hand. Years of sharing a room did nothing for Sam as far as keeping quiet. 

 

Both sank into the couch and panted for a while as the video continued to play. Dean moved first. He leaned forward to stop the video and grab a napkin. He cleaned himself up with it and absently tried to hand it to Sam.

 

Sam was grossed out, “Dude, I'm not sharing a spunk napkin with you.”

  
Dean reacted quickly. He laughed and shoved it against Sam's face as he yanked his pants up. He managed to scurry to the bathroom and close the door while Sam was tangled up in his own jeans. Sam screaming and cursing through the door only made him laugh harder. 


	2. Chapter 2

“Dude! I think we've got a fantastic - one time only, like EVER! Offer-”

“Dean, no. I'm exhausted.” Sam wanted to add that all he was interested in is something resembling a flat surface for three to five hours of sleep. Instead he was at a bar with Dean to ‘celebrate’ that they hadn't been killed or popped by the police as they tore out of town on the latest hunt. Said hunt was three states behind them and Sam's adrenaline subsided after two.

“You didn't even listen to the offer!”

“What are you an infomercial now?”

Dean huffed and ignored Sam's shitty attitude. “Hot redhead at your eight o'clock -”

“The one you were talking to. I saw her. Everyone did. You two were practically dry humping on the bar -”

“Shut it, judgey!” Dean leaned closer. "So she's got an idea and a friend,” Sam rolled his eyes but didn't interrupt him this time. “Apparently, she's got a wild streak and a friend with the same attitude.” Dean wagged his eyebrows for emphasis.

Sam couldn't help it this time. “Great. Have fun but give me the keys.”

“No!” Dean grinned, "Wild ladies of whatever the fuck town we're in want to fuck us. Looking for a package deal or something.”

Sam really was exhausted. He wouldn’t admit it to Dean, but at this point he was not even confident he could get it up. Forget about fucking a girl at the level that Dean should be watching! “I'm beat and I told you that I just want to sleep _two hours_ ago when we got here…”

Dean turned to motion to the girl at the bar and continued. “You are being a brat, Sam! You're also not quite getting the offer: they want to fuck us.”

“Dean, believe it or not, I'm used to girls wanting to fuck me -”

“They. Fuck. Us.” Dean waited for the gears to click but wasn't patient enough. “As in, they've got hardware and want to be the ones to rail us.” God, Sam was dense when he was tired. Dean couldn't believe he had to clarify when this topic only recently came up between them. Dean cleared his throat and whispered, “Strap ons, you fucking dingus! Her and her friend want to bang us at the same time.”

Oh. While it was a wonderful idea, there was still the matter that Sam was not in the mood… yet. “I don't see a friend. How do you know this isn't a setup?”

“A setup for _what?_ Chicks with fake dicks is not the thing to lure most guys in!”

Fine. He had a point. Sam had no time to respond. The redhead walked over to their table with two beers and plunked a fresh beer down in front of Dean. She plastered herself to his side and ran a hand over his chest. She had a husky voice when she spoke, “So do we have a deal?”

Dean groaned, “Not yet. Sam here is being difficult.”

She gave an exaggerated, fake pout and turned her attention to Sam. “That's a shame.”

Sam let out a long sigh. “I didn't say ‘no.’ I just need more information… and at least one more drink.”

She gave a wolfish smile to him. “I'll get that for you, darling. Just wait right here.”

As soon as her back was to them, Sam was dumping holy water in the beer she left on the table. Dean gave him an incredulous look, “Dude! Be a little more subtle!”

Sam snapped quickly, “We don't have time for subtle and I certainly don't have time to get butt raped by a demon because you were too busy getting your tongue down her throat!”

Dean slapped Sam's arm down and pinned it to the table, “I already tested her with holy water and silver. Do you think I'm stupid?”

Sam sniped back, “I think you're stupid when you're thinking with your dick.” He wrenched his arms away and pocketed his flask. Dean continued to glare at him.

The redhead returned with a beer for Sam and extended her hand, “I'm Sara, by the way.”

Sam shook her hand, “Sam.”

Sara smiled, “So Sam, what kind of information do you need? My friend and I would love to play with you and your brother.” Sam could tell that she was rubbing Dean's dick through his jeans across the table from him.

Dean tried to sound composed when he added, “Yeah Sam, let's make this happen…”

Sam's brain was racing. He gathered his thoughts before answering. “First off, I don't see a friend with you. Who is she? Where is she? And is she really going to agree to this without seeing us first?”

Sara smirked, “My friend Dawn is at work right now. She gets out between 10:30 and 11.” Sam spared a glance at the clock, _great it's only 9:15. Fucking timezones._ She continued, “We don't get to play nearly as much as we'd like to. She trusts my judgment when it comes to finding… suitable men for the job.”

Dean piped up, “Show him her picture.”

She reached into her too - tight jeans and got her cellphone out. She scanned through her pictures and flipped the screen around to Sam. Suddenly, Sam's mouth was dry because it was certainly not a tame picture: lithe brunette, attractive, clad in an all black vinyl catsuit. She was holding Japanese bondage ropes… not that Sam spent countless hours jerking off to porn with those in it. Not at all.

Sam cleared his throat, “And um… where would we be doing this?”

Sara could tell she was wearing him down. “There's a playroom about twenty minutes from here. It is members only and we can get you in. We would have a semi-private room, but to be perfectly honest I prefer an audience.” _No wonder her and Dean had hit it off: exhibitionists._ “Guys that look like you would definitely get some people watching.”

Sam wasn't a big fan of people watching him, save for Dean once in awhile. It was not a deal breaker but he would prefer that he was not objectified and scrutinized by strangers. At this point Sam could practically hear Dean mentally screaming at him. He played it coy just to piss Dean off. “So realistically how soon would this happen?” Yep, Dean was definitely screaming ‘Fuck you’ repeatedly in his head.

She thought it over. “By the time she gets out of work and changed… and gets over there… I don't know, midnight?”

Dean glared daggers at Sam. Sam acted like he was thinking it over. “And how late is the place open?”

She leaned closer to him, “As late as we want.”

Sam waited just long enough to make Dean almost punch him. “Okay, I'm in.”

Dean jumped out of his chair and clapped him on the shoulder, “There you go, Sammy!”

Sam decidedly ignored Dean's boner from Sara’s attention at his eye level, “Give me the keys, I'm going to rest in the car.”

 

* * *

 

They arrived at the nondescript building in an industrial park around 11:30. They shared Dean's bottle of whiskey, mostly to calm Sam's nerves. After Sam had left the bar, Dean learned that the club was next to a power tool manufacturing facility. Apparently the owner managed it under in conjunction with his other business; an unassuming person would be none-the-wiser about what happened there. Dean was impressed with the subtlety of the entire operation.

The women arrived around 12:15. As they get out of their car, Sam noted that both were wearing vinyl but have coats on to give the illusion of modesty. Both were carrying duffel bags that Sam assumed to have gear inside. They went to the side door of the building where two men in suits greeted them. Sara vouched for Sam and Dean and they were lead through a maze of hallways to a lobby area. There were a handful of people in various states of undress milling about. A third woman pulled their dates aside for a quick discussion. Sam tried not to fidget under the scrutiny of the strangers in the room. The woman took the women's coats and approached the brothers. They both covered their gawking well. Sara was in a full red vinyl catsuit with a black waist corset while Dawn is in a military style vinyl jacket with g-string and thigh high boots.

The new woman looked the brothers up and down, “You two are violating the dress code here.”

Dawn tisked, “Not off to a good start boys. Nancy, if they strip will you overlook it?” Sam blushed profusely while Dean grinned like an idiot.

Nancy softened for a moment, “Do you use the standard color system or do you have a different set of safe words?”

Dean answered quickly, “Impala for red.” ‘ _Really?’_ Sam thought. Dean added, “And all green if you want me to strip right here.”

Sam interjected in a less than confident voice, “I can't do this.” Public nudity, being on the receiving end of sex with strangers watching, the subtle smell of bleach and sanitizer in this place... maybe he should have drank more… the whole audience thing - and what if some demon or other less than friendly thing was in here? How the hell were they supposed to test for that? The rest of the group stared at him. Sam quietly added, “It's just the whole… there's a lot of people here.”

Nancy silently took them to a room with no door around the corner. Sam and Dean entered first. Dean tried to make eye contact with Sam but Sam was avoiding it. Dean asked, “Are you okay, Sam?”

Sam felt panic starting to set in. “No.”

Dean internally cringed because Sam sounded like he did when they were kids and he wasn't going to admit that he was spooked by something. At least Sam admitted he wasn't okay. That was a start. Dean forced himself to lower his voice as much as he could in this loud place, “What's wrong? Is there something I can do?”

Sam finally looked at Dean. Sam sounded defeated when he spoke, “This is a bad idea. What if there's someone here who actually has it out for us? It's just not safe for us to be out in the open and vulnerable like this. I know I was into this at the bar but I just -”

Dean didn't hesitate. He turned to their dates, who were standing just outside the room, and firmly stated, “We're leaving.”

Dawn commented, “Your loss,” as Dean pushed Sam past her.

Sara walked alongside Dean. She asked, “Is this a full deal breaker?”

Dean turned to her, “Yes. You said it was a package deal and I'm not gonna ask him to change his mind.” Dean put it on Sam but mentally kicked himself for not thinking this through.

She stopped pursuing when they got close to the parking lot. Sam noticed she only seemed disappointed, not annoyed, by the situation. They got to the Impala and climbed in. Dean started the engine and pulled out of the space. Sam quietly spoke again, “Sorry, Dean.”

Dean shot him a look that Sam couldn't get a read on, “You don't need to apologize, Sam. You never say no to anything like this. I shouldn't have put you in that position.” Dean pulled into a parking lot in a neighboring lot and cut the engine. Sam looked confused and Dean told him, “I ain't driving further than necessary. I just wanted to get you out of there. Give me another twenty or thirty and I'll be good to hit the road.” He reached for the cooler in the back seat and pulled out two bottles of water. He handed one to Sam and cracked his own open. He could feel Sam brooding next to him. After he downed half the bottle he finally looked at Sam. “Hey, don't do that moping thing you do over this.”

“I'm not moping,” Sam was still looking out the window away from Dean.

Dean huffed, “I'm serious. We usually talk this stuff out beforehand and I sprung this on you. You are right. We shouldn't purposely make ourselves that open to be attacked. It kinda didn't occur to me that you would have reservations about being watched with how much we've done though.” Sam didn't say that last part out loud but Dean picked it up anyway.

Sam finally looked at Dean, “They're not you.”

Dean squeezed his shoulder and took another gulp of water, “I know.”

Sam looked Dean over, “Are you sure you'll be good to drive in a few minutes?”

Dean rolled his eyes, “Want me to take a field sobriety test? You drank almost all of the booze before. You owe me a new one, by the way.”

Sam grumbled, “Fine.” Sam had no way to prove whether or not Dean was lying. Dean wouldn't risk his Baby though so Sam trusted his judgement.

After a half hour in silence Dean turned the key in the ignition and began to drive toward to highway. There was no specific destination in mind so he went with the general direction of northeast. They would find a motel along the way or just sleep in the car when Dean became too tired to continue. He made sure they were at a decent speed when he cracked a grin and asked, “So does this mean I get a list of all your hard limits or something?” Dean was already laughing before he got the entire question out.

Sam glared at him, “No.” Sam knew Dean waited to make that crack until they were driving too fast for Sam to storm off or threaten that he would get out of the car. “You're an asshole.”

Dean was still laughing and but composed himself when he added, “Come on! Even under ideal circumstances you probably would have thrown up a red flag at some point on that. I just need to know what I'm working with here.”

Sam’s glare intensified, “I hate you.”

Dean kept on it, “You love me and you know it!” Dean took a more serious tone after composing himself, “We're good, right?”

Sam sighed and looked at Dean, “Yeah. We're fine.”

Dean responded, “Good. We won't attempt that again. What's our next sex adventure?”

Sam was back to being annoyed, “Nothing if you don't stop being a jerk.”

Dean rolled his eyes, “Yeah right. You can't hold out on me forever, bitch.”

Sam grumbled, “Let me sleep on it."

  
Dean smirked but decided to shut up about it. He was already scheming up a way to get Sam in on the action again.

**Notes for the Chapter:**

> Originally this fic was going to have the boys go through with everything but I changed my mind. I'm considering finishing the other ending and posting it separately. 
> 
> Kudos and comments are always greatly appreciated.


End file.
